Details of the Drug

General Information of Drug (ID: DMAKIDV)

Drug Name
Dydrogesterone
Synonyms
Dehydrogesterone; Didrogesterona; Didrogesterone; Diphaston; Dufaston; Duphaston; Duvaron; Dydrogesterona; Dydrogesteronum; Gestatron; Gynorest; Hydrogesterone; Hydrogestrone; Isopregnenone; Prodel; Retrone; Terolut; Didrogesterone [DCIT]; Solvay Brand of Dydrogesterone; DELTA6-Retroprogesterone; Duphaston (TN); Dydrogesterona [INN-Spanish]; Dydrogesteronum [INN-Latin]; Gynorest (TN); Delta(6)-Retroprogesterone; Delta(sup 6)-Retroprogesterone; Retro-6-dehydroprogesterone; Dydrogesterone (JP15/USP/INN); Dydrogesterone [USAN:INN:BAN:JAN]; Pregna-4,6-diene-3,20-dione, (9-beta,10-alpha)-(9CI); (8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one; (9-beta,10-alpha)-Pregna-4,6-diene-3,20-dione; (9beta,10alpha)-pregna-4,6-diene-3,20-dione; 10alpha-Isopregnenone; 6 Dehydro 9 beta 10 alpha progesterone; 6-Dehydro-9 beta-10 alpha-progesterone; 6-Dehydro-9.beta.,10.alpha.-progesterone; 6-Dehydro-9beta,10alpha-progesterone; 6-Dehydro-retro-progesterone; 6-Dehydroretroprogesterone; 9-.beta.,10.alpha.-Pregna-4,6-diene-3,20-dione; 9-beta,10-alpha-Pregna-4,6-diene-3,20-dione; 9-beta,10alpha-Pregna-4,6-diene-3,20-dione; 9.beta.,10.alpha.-Pregna-4,6-diene-3,20-dione; 9beta,10alpha-Pregna-4,6-diene-3,20-dione; 9beta,10alpha-Pregna-4,6-diene-3,20-dione (8CI)
Indication
Disease Entry ICD 11 Status REF
Menstrual disorder GA20.3 Approved [1]
Therapeutic Class
Progesterones
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 312.4
Logarithm of the Partition Coefficient (xlogp) 3.8
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 5 - 7 hours [2]
Metabolism
The drug is metabolized to a 20-dihydrodydrogesterone (DHD) metabolite []
Chemical Identifiers
Formula
C21H28O2
IUPAC Name
(8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES
CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@@H]3[C@H]2C=CC4=CC(=O)CC[C@@]34C)C
InChI
InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1
InChIKey
JGMOKGBVKVMRFX-HQZYFCCVSA-N
Cross-matching ID
PubChem CID
9051
ChEBI ID
CHEBI:31527
CAS Number
152-62-5
DrugBank ID
DB00378
TTD ID
D0F1UL
INTEDE ID
DR0556
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Progesterone receptor (PGR) TTUV8G9 PRGR_HUMAN Agonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
17-beta-hydroxysteroid dehydrogenase type 2 (HSD17B2) OT3K7HY5 DHB2_HUMAN Gene/Protein Processing [5]
3-oxo-5-alpha-steroid 4-dehydrogenase 1 (SRD5A1) OTQRET2B S5A1_HUMAN Gene/Protein Processing [5]
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Gene/Protein Processing [5]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [5]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [5]
Interferon gamma (IFNG) OTXG9JM7 IFNG_HUMAN Gene/Protein Processing [6]
Interleukin-4 (IL4) OTOXBWAU IL4_HUMAN Gene/Protein Processing [6]
Interleukin-6 (IL6) OTUOSCCU IL6_HUMAN Gene/Protein Processing [6]
Progesterone-induced-blocking factor 1 (PIBF1) OTCBT1A1 PIBF1_HUMAN Gene/Protein Processing [6]
Tumor necrosis factor (TNF) OT4IE164 TNFA_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Menstrual disorder
ICD Disease Classification GA20.3
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Progesterone receptor (PGR) DTT PGR 3.26E-38 -3.79 -2.5
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 2.20E-02 -1.08E-01 -2.31E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2878).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Dienogest is a selective progesterone receptor agonist in transactivation analysis with potent oral endometrial activity due to its efficient pharm... Steroids. 2008 Feb;73(2):222-31.
4 Dydrogesterone metabolism in human liver by aldo-keto reductases and cytochrome P450 enzymes. Xenobiotica. 2016 Oct;46(10):868-74.
5 Progestin effects on expression of AKR1C1-AKR1C3, SRD5A1 and PGR in the Z-12 endometriotic epithelial cell line. Chem Biol Interact. 2013 Feb 25;202(1-3):218-25.
6 Modulation of cytokine production by dydrogesterone in lymphocytes from women with recurrent miscarriage. BJOG. 2005 Aug;112(8):1096-101. doi: 10.1111/j.1471-0528.2005.00633.x.